Search Islamorada villas with a pool

Our top choices for a great stay

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and a garden. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery ...
10/10 Exceptional! (1 review)
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windley Key Fossil Reef Geological State Park and Rain ...
10/10 Exceptional! (12 reviews)
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Islamorada Brewery & Distillery and Keys History & ...
10/10 Exceptional! (2 reviews)
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Island pool home awaits in Islamorada's Port Antigua

Island pool home awaits in Islamorada's Port Antigua

Book a stay at this family-friendly villa in Islamorada. Enjoy free WiFi, private pools, and a water park. Popular attractions Sunset Drive Beach and Anne's ...
10/10 Exceptional! (5 reviews)
Island pool home awaits in Islamorada's Port Antigua
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Matecumbe United Methodist Church and Keys History ...
10/10 Exceptional! (2 reviews)
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.

Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.

Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and patios. Popular attractions Windley Key Fossil Reef Geological State Park and ...
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool

Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool

Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and air conditioning. Popular attractions Rain Barrel Village and Islamorada County ...
Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery ...
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery ...
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Turtle Nest Estate in Islamorada

Turtle Nest Estate in Islamorada

2 out of 5
Stay at this villa in Islamorada. Enjoy a full-service spa. Popular attractions Robbie’s of Islamorada and Sunset Drive Beach are located nearby.
Turtle Nest Estate in Islamorada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.